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Kyle Stewart

1461 Articles

Pittsburgh, PA
Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, Travel Codex, PenAndPassports, Live And Lets Fly and many other media outlets. He is also co-founder of Scottandthomas.com, a travel agency that delivers "Travel Personalized." He focuses on using miles and points to provide a premium experience for his wife, daughter, and son. Email: sherpa@thetripsherpa.comEmail: sherpa@thetripsherpa.com
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Amazon

Affordable Vacation Homes From Amazon Prime?

Kyle Stewart Posted onJuly 7, 2019November 14, 2023 4 Comments
a house with a deck and a patio

It feels like Amazon Prime delivers just about everything these days including tiny home kits. When paired with surprisingly reasonably-priced vacation property, owning a vacation home is more affordable than I would have thought. If you are considering booking travel or signing...

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ChaseCredit CardsNewsUnited Airlines

Banks May Force United, Others To Change Loyalty Programs

Kyle Stewart Posted onJune 30, 2019November 14, 2023 37 Comments
a white airplane on a runway

Airlines are dependent on banks to buy award miles with exclusive credit card deals but at least one relationship (Chase and United Airlines) is struggling. Could this be the moment that airlines reverse course? If you are considering booking travel or signing...

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News

Toronto Raptors Player Gets Drake’s Free Jet Deal

Kyle Stewart Posted onJune 30, 2019September 14, 2021 1 Comment
kawhi leonard

The Canadian rapper, Drake, announced that he had secured a 767 for his personal flying. The deal was likely not as advertised to the public and media’s dismay. Now, Toronto Raptors small forward Kawhi Leonard has one too. If...

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Avianca

Should You Be Worried About Your LifeMiles? They Don’t Think So

Kyle Stewart Posted onJune 30, 2019September 14, 2021 6 Comments
Avianca

LifeMiles, the loyalty program from Colombian carrier, Avianca issued an email this week to reassure members that their miles are safe. But are your LifeMiles safe? I’m not so sure and, clearly, neither is Avianca.  If you are considering booking travel or signing...

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American AirlinesNews

American Airlines Mechanics Making Their Mark

Kyle Stewart Posted onJune 23, 2019September 14, 2021 15 Comments
a close-up of a person's foot

I have written previously about dissatisfied American Airlines employees, recently the mechanics have made the most noise. Now, the results of their actions have begun to show.  If you are considering booking travel or signing up for a new credit card please click...

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HiltonHotelsHyatt

Rollover Credits Move My Remaining Stays to Hilton Over Hyatt

Kyle Stewart Posted onJune 23, 2019September 14, 2021 10 Comments
hotel sign and stranger

This year I have top tier status with several hotel chains but re-qualifying for next year will place an emphasis on Hilton going forward over Hyatt, my focus program. If you are considering booking travel or signing up for a new credit...

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BusinessFamily Travel

Bringing Family On Business Trips

Kyle Stewart Posted onJune 23, 2019September 14, 2021 7 Comments
Mother and daughter walk in Colombia

The more I travel for work, the more I long to have my family with me. But just what does that look like and what are the ethical implications of bringing the family along on business trips? If you...

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American AirlinesElite StatusNewsUnited Airlines

Premium Economy Best Way to Qualify For Status

Kyle Stewart Posted onJune 16, 2019November 14, 2023 15 Comments
United A320 at gate

Last week I wrote about the need for a status run on United to maintain my 1K status. It’s clear that Premium Economy is the best way to re-qualify on seemingly any US airline. If you are considering booking travel or signing...

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American AirlinesNews

Mechanics Slowdown Makes American Airlines Safer, Not Enjoyable

Kyle Stewart Posted onJune 16, 2019September 14, 2021 41 Comments
a close-up of a person's foot

Mechanics at American Airlines have been negotiating their contract (and have been out of contract) for years. Work slowdowns for maintenance concerns, however, make the carrier safer, even if inconvenient. If you are considering booking travel or signing up for a new...

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American AirlinesNews

American Airlines Executives Throw Away Cash, Buy More AAL Stock

Kyle Stewart Posted onJune 9, 2019September 14, 2021 20 Comments
American Airlines A330

This week American Airlines senior executives loaded their personal coffers with even more American Airlines stock (AAL). Was it a sign of hubris or idiocy?  If you are considering booking travel or signing up for a new credit card please click here. Both support...

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Hyatt

Hyatt Globalist My Concierge Details Exposed, Reinforcements Coming

Kyle Stewart Posted onJune 9, 2019September 14, 2021 20 Comments
hotel bell sized

Hyatt Hotels reward Globalists with a perk called My Hyatt Concierge. Few details about the program have been revealed, but new information suggests solutions to the program’s woes are in store. If you are considering booking travel or signing up for a...

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Mileage PlusMileage RunsUnited Airlines

Once Again, I Must Status Run on United

Kyle Stewart Posted onJune 9, 2019September 14, 2021 25 Comments
United IRROPS

Depending on my personal and business trips during the course of a year, I sometimes must fly unnecessary flights simply to retain my status. Again, this year I must status run for United 1K.  If you are considering booking travel or signing...

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American AirlinesNews

Can American Airlines CEO Doug Parker Survive The Summer?

Kyle Stewart Posted onJune 2, 2019November 14, 2023 94 Comments
American Airlines A330

American Airlines has had difficulty with employee groups lately and morale is low. But with the stock price at an all-time low and the potential for employee action, can CEO Doug Parker possibly survive the summer? If you are...

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NewsUber

Uber Banning US, Canadian Riders With Low Scores

Kyle Stewart Posted onJune 2, 2019November 14, 2023 11 Comments
Uber black car beer estimate

Uber has expanded its program to boot US and Canadian riders from their app who have substandard star ratings as they have in other countries. On the surface, this plan makes sense but it’s imperfect and may not work...

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American AirlinesBusinessDelta Air Lines

Who Keeps Business Travel Booking Incentives?

Kyle Stewart Posted onJune 2, 2019November 14, 2023 1 Comment
road warrior

Travel arrangers within a business may earn incentives similarly to frequent flyers for using a particular airline or hotel chain. But if frequent flyer miles go to the employee even when the business pays, should the booking incentives go...

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AirbnbMarriottNews

Marriott Launches Tone Deaf Airbnb Competitor

Kyle Stewart Posted onMay 26, 2019September 14, 2021 26 Comments
hotel sign and stranger

Marriott didn’t think of Airbnb and the Homeshare market as much competition but has since launched a Homeshare program. It only goes to prove that their leadership is tone deaf, out of touch and still just doesn’t get it. ...

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Chase

Chase Gets Reward Programs, Why Don’t Others?

Kyle Stewart Posted onMay 26, 2019November 14, 2023 8 Comments
sized Singles Day

This week I had three interactions with three banks and it became clear that Chase knows how to motivate me because Chase knows how rewards programs work, why is it so hard for everyone else?  If you are considering booking...

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Hyatt

Hyatt Partnership with SLH Smart Solution

Kyle Stewart Posted onMay 26, 2019September 14, 2021 3 Comments
hotel bell sized

Hyatt has rolled out a partnership with SLH (Small Luxury Hotels of the World) to expand the footprint of their loyalty program. It was the smartest solution to their biggest problem, the number of properties. If you are considering booking...

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News

Drake Bought a Plane But It Wasn’t $220 Million

Kyle Stewart Posted onMay 19, 2019September 14, 2021 17 Comments
drake plane

The Canadian rapper, Drake, showcased his new private jet – a Boeing 767-3oo freighter converted to opulence. However, the media outlets weren’t even close when suggesting the costs. If you are considering booking travel or signing up for a new credit card please...

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AirportsAlaska AirlinesUnited Airlines

My Mother Loves Seattle’s Second Airport

Kyle Stewart Posted onMay 19, 2019November 14, 2023 5 Comments
a room with computers and a screen

My mother visited her sister who lives in Everett, WA. Instead of flying into SEATAC she tried out Seattle’s second airport north of Seattle in Everett, WA (Paine Field). She loved it as does nearly everyone.  If you are...

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